Top St Petersburg Sailing Tours

While in Treasure Island, see the beautiful area without getting caught in the crowds on land. This Treasure Island Sailing Experience lets you go on a small-group cruise around either the Gulf of Mexico or Boca Ciega Bay. You can bring your own drinks as a cooler is provided for cruiser goers to use, or you can enjoy the included soda and bottled water.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

Take a relaxed sunset cruise launching from St. Pete Beach and view a different side of the city on this shared small group boat ride. Although it’s shared, the passenger count is kept low to create a semi-intimate experience as you cruise through residential canals to view local mansions. As you pass by Tierra Verde, you might see dolphins swimming near your boat. Bottled water is provided, as well as blankets in the cooler months.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

Look for dolphins around Boca Ciega Bay in St. Pete Beach on a cruise in the Tampa Bay Area. Continue into the Gulf of Mexico to visit Shell Key island, a wildlife preserve where you can snorkel, swim, or collect shells on the beach. Depending on the season, you might spot dolphins, manatees, rays, and a variety of seabirds. This family-friendly tour offers both a late morning and afternoon departure, making it easy to suit your schedule.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

If you're looking for a place to watch the sun set over Florida's stunning water, but don't want to just sit dockside, this Gulf of Mexico Sunset Cruise from Madeira Beach takes you out on the water to do just that. Bring your own alcohol (or non-alcoholic drinks) and enjoy the sunset over the Gulf of Mexico.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.

Your own private 42’ Bali 4.2 catamaran with no shared crowds — just your group, captain, and crew. Sweet Escape offers a premium all-inclusive charter experience from St. Petersburg with fuel, ice, bottled water, soft drinks, light snacks, Bluetooth music, paddleboards, floating mat, snorkel gear, towels, shaded seating, and spacious lounge areas included. Each trip is customized around your group’s priorities, whether you want scenic cruising, swimming, relaxing, sightseeing, sunset views, or a special celebration on the water.